How to Pick a Career (That Actually Fits You)

This is a post about something I’ve been wanting to write about forever: careers. Society tells us a lot of things about what we should want in a career and what the possibilities are—which is weird because I’m pretty sure society knows very little about any of this. When it comes to careers, society is like your great uncle who traps you at holidays and goes on a 15-minute mostly incoherent unsolicited advice monologue, and you tune out almost the whole time because it’s super clear he has very little idea what he’s talking about and that everything he says is like 45 years outdated. Society is like that great uncle, and conventional wisdom is like his rant. Except in this case, instead of tuning it out, we pay rapt attention to every word, and then we make major career decisions based on what he says. Kind of a weird thing for us to do.

This post isn’t me giving you career advice really—it’s a framework that I think can help you make career decisions that actually reflect who you are, what you want, and what our rapidly changing career landscape looks like today. You’re not a pro at this, but you’re certainly more qualified to figure out what’s best for you than our collective un-self-aware great uncle. For those of you yet to start your career who aren’t sure what you want to do with their lives, or those of you currently in the middle of your career who aren’t sure you’re on the right path, I hope this post can help you press the reset button on your thought process and get some clarity.

Finally, it feels very good to put this post up. It’s been way, way too long. The last year has been pretty frustrating for me and anyone who likes Wait But Why—a lot of build-up of ideas with none of the satisfying release of those ideas on the blog (most of my last year has been spent working on another, way longer post). I’m hoping this WBW Dark Ages era is nearing its end, because I miss hanging out here. Thanks, as always, to the small group of ridiculously generous, ridiculously patient patrons who have stuck with us through such a slow period.

– Tim

PDF: If you want to print this post or read it offline, the PDF is probably the way to go. You can buy it here.

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Your Life Path So Far

For most of us, childhood is kind of like a river, and we’re kind of like tadpoles.

We didn’t choose the river. We just woke up out of nowhere and found ourselves on some path set for us by our parents, by society, and by circumstances. We’re told the rules of the river and the way we should swim and what our goals should be. Our job isn’t to think about our path—it’s to succeed on the path we’ve been placed on, based on the way success has been defined for us.

For many of us—and I suspect for a large portion of Wait But Why readers—our childhood river then feeds into a pond, called college.1 We may have some say in which particular pond we landed in, but in the end, most college ponds aren’t really that different from one another.

In the pond, we have a bit more breathing room and some leeway to branch out into more specific interests. We start to ponder, looking out at the pond’s shores—out there where the real world starts and where we’ll be spending the rest of our lives. This usually brings some mixed feelings.

And then, 22 years after waking up in a rushing river, we’re kicked out of the pond and told by the world to go make something of our lives.

There are a few problems here. One is that at that moment, you’re kind of skill-less and knowledge-less and a lot of other things-less:

But before you can even address your general uselessness, there’s an even bigger issue—your pre-set path ended. Kids in school are kind of like employees of a company where someone else is the CEO. But no one is the CEO of your life in the real world, or of your career path—except you. And you’ve spent your whole life becoming a pro student, leaving you with zero experience as the CEO of anything. Up to now, you’ve only been in charge of the micro decisions—”How do I succeed at my job as a student?”—and now you’re suddenly holding the keys to the macro cockpit as well, tasked with answering stressful macro questions like “Who am I?” and “What are the important things in life?” and “What are my options for paths and which one should I choose and how do I even make a path?” When we leave school for the last time, the macro guidance we’ve become so accustomed to is suddenly whisked away from us, leaving us standing there holding our respective dicks, with no idea how to do this.

Then time happens. And we end up on a path. And that path becomes our life’s story.

At the end of our life, when we look back at how things went, we can see our life’s path in its entirety, from an aerial view.

When scientists study people on their deathbed and how they feel about their lives, they usually find that many of them feel some serious regrets. I think a lot of those regrets stem from the fact that most of us aren’t really taught about path-making in our childhoods, and most of us also don’t get much better at path-making as adults, which leaves many people looking back on a life path that didn’t really make sense, given who they are and the world they lived in.

So this is a post about path-making. Let’s take a 30-minute pre-deathbed pause to look down at the path we’re on, and ahead at where that path seems to be going, and make sure it makes sense.

The Cook and the Chef—Revisited

In the past, I’ve written about the critical distinction between “reasoning from first principles” and “reasoning by analogy”—or what I called being a “chef” vs. being a “cook.” Since writing the post, I notice this distinction everywhere, and I’ve thought about it roughly 2 million times in my own life.

The idea is that reasoning from first principles is reasoning like a scientist. You take core facts and observations and use them to puzzle together a conclusion, kind of like a chef playing around with raw ingredients to try to make them into something good. By doing this puzzling, a chef eventually writes a new recipe. The other kind of reasoning—reasoning by analogy—happens when you look at the way things are already done and you essentially copy it, with maybe a little personal tweak here and there—kind of like a cook following an already written recipe.

A pure verbatim recipe-copying cook and a pure independently inventive chef are the two extreme ends of what is, of course, a spectrum. But for any particular part of your life that involves reasoning and decision making, wherever you happen to be on the spectrum, your reasoning process can usually be boiled down to fundamentally chef-like or fundamentally cook-like. Creating vs. copying. Originality vs. conformity.

Being a chef takes a tremendous amount of time and energy—which makes sense, because you’re not trying to reinvent the wheel, you’re trying to invent it for the first time. Puzzling your way to a conclusion feels like navigating a mysterious forest while blindfolded and always involves a whole lot of failure, in the form of trial and error. Being a cook is far easier and more straightforward and less icky. In most situations, being a chef is a terrible waste of time, and comes with a high opportunity cost, since time on Earth is immensely scarce. Right now, I’m wearing J. Crew jeans and a plain t-shirt and a hoodie and Allbirds shoes, because I’m trying to conform. Throughout my life, I’ve looked around at people who seem kind of like me and I’ve bought a bunch of clothes that look like what they wear. And this makes sense—because clothes aren’t important to me, and they’re not how I choose to express my individuality. So in my case, fashion is a perfect part of life to use a reasoning shortcut and be a cook.2

But then there are those parts of life that are really really deeply important—like where you choose to live, or the kinds of friends you choose to make, or whether you want to get married and to whom, or whether you want to have kids and how you want to raise them, or how you set your lifestyle priorities.

Career-path-carving is definitely one of those really really deeply important things. Let’s spell out the obvious reasons why:

Time. For most of us, a career (including ancillary career time, like time spent commuting and thinking about your work) will eat up somewhere between 50,000 and 150,000 hours. At the moment, a long human life runs at about 750,000 hours. When you subtract childhood (~175,000 hours) and the portion of your adult life you’ll spend sleeping, eating, exercising, and otherwise taking care of the human pet you live in, along with errands and general life upkeep (~325,000 hours), you’re left with 250,000 “meaningful adult hours.”3 So a typical career will take up somewhere between 20% and 60% of your meaningful adult time—not something to be a cook about.

Quality of Life. Your career has a major effect on all the non-career hours as well. For those of us not already wealthy through past earnings, marriage, or inheritance, a career doubles as our means of support. The particulars of your career also often play a big role in determining where you live, how flexible your life is, the kinds of things you’re able to do in your free time, and sometimes even in who you end up marrying.

Impact. On top of your career being the way you spend much of your time and the means of support for the rest of your time, your career triples as your primary mode of impact-making. Every human life touches thousands of other lives in thousands of different ways, and all of those lives you alter then go on to touch thousands of lives of their own. We can’t test this, but I’m pretty sure that you can select any 80-year-old alive today, go back in time 80 years, find them as an infant, throw the infant in the trash, and then come back to the present day and find a countless number of things changed. All lives make a large impact on the world and on the future—but the kind of impact you end up making is largely within your control, depending on the values you live by and the places you direct your energy. Whatever shape your career path ends up taking, the world will be altered by it.

Identity. In our childhoods, people ask us about our career plans by asking us what we want to be when we grow up. When we grow up, we tell people about our careers by telling them what we are. We don’t say, “I practice law”—we say, “I am a lawyer.” This is probably an unhealthy way to think about careers, but the way many societies are right now, a person’s career quadruples as the person’s primary identity. Which is kind of a big thing.

So yeah—your career path isn’t like my shitty sweatshirt. It’s really really deeply important, putting it squarely in “Definitely absolutely make sure to be a chef about it” territory.

Your Career Map

Which brings us to you. I don’t know exactly what your deal is. But there’s a good chance you’re somewhere in one of the blue regions—

Whether you’re yet to start your career or well into it, somewhere in the back of your mind (or maybe in the very front of it) is a “Career Plans” map.

We can group map holders into three broad categories—each of which is well-represented in the river, in the pond, standing on the shore, and at every stage of adult life.

One group of people will look at the map and see a big, stressful question mark.

These are people who feel indecisive about their career path. They’ve been told to follow their passion, but they don’t feel especially passionate about anything. They’ve been told to let their strengths guide them, but they’re not sure what they’re best at. They may have felt they had answers in the past, but they’ve changed and they’re no longer sure who they are or where they’re going.

Other people will see a nice clear arrow representing a direction they feel confident is right—but find their legs walking in a different direction. They’re living with one of the most common sources of human misery, a career path they know in their heart is wrong.

The lucky ones feel they know where they want to go and believe they’re marching in that direction.

But even these people should pause and ask themselves, “Who actually drew this arrow? Was it really me?” The answer can get confusing.

I’m pretty sure all of these people would benefit from a moment of career path reflection.

The Okay But Why Do You Think You Can Help Me With My Career Reflection You Draw Stick Figures for a Living Blue Box

Extremely fair question. One thing I always ask myself as I pick topics to write about is, “Am I qualified to write about this?” Here are the reasons I decided to take on this topic:

1) I have spent most of the last 20 years in a perpetual state of analyzing my own career path.

2) My path has taken a lot of turns—from wanting to be a movie star when I was 7 to wanting to be the president when I was 17 to wanting to write film scores when I was 22 to wanting to be an entrepreneur when I was 24 to wanting to write musicals when I was 29 to most recently wanting to be a writer-ish guy.

3) After being pretty all over the place about my career path for most of my life, I actually love my job now. That’s always subject to change, but being able to look at the decision-making processes that led me to confusing or frustrating places, side by side with the decisions that led me to a more fulfilling place, has offered me some wisdom on where people tend to go wrong.

4) On top of having my own story to look at, I’ve had a front-row seat for the stories of my dozen or so closest friends. My friends seem to share my career path obsessiveness, so between observing their paths and talking with them about those paths again and again along the way, I’ve broadened my views on the topic, which helps me to distinguish between the lessons that are my-life specific and those that are more universal.

5) Finally, this isn’t a post about which careers are better or worse than others or which career values are more or less meaningful—there are lots of social scientists and self-help authors out there with good data on that, and I’m not one of them. It’s instead a framework that I think can help a career-path reflector better see their own situation, and what really matters to them, clearly and honestly. This framework has worked really well for me, so I think it can probably be helpful for other people too.

Now that you’ve taken a fresh look at your Career Plans map, along with whatever arrow may or may not be on it, put it down and out of sight. We’ll come back to it at the end of the post. It’s time now for a deep dive—let’s think about this from scratch. From first principles.

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In the cook-chef post, I designed a simple framework for how a chef makes major career choices. At its core is a simple Venn diagram.

The first part of the diagram is the Want Box, which contains all the careers you find desirable.

The second part of the diagram is the Reality Box. The Reality Box is for the set of all careers that are realistic to potentially achieve—based on a comparison, in each case, between your level of potential in an area and the general difficulty of achieving success in that area.

The overlapping area contains your optimal career path choices—the set of arrows you should consider drawing on your Career Map. We can call it the Option Pool.

This is straightforward enough. But actually filling in these boxes accurately is way harder than it looks. For the diagram to work, it has to be as close to the truth as possible, and to get there, we have to lift up the hood of our subconscious and head down. Let’s start with the Want Box.

Deep Analysis, Part 1: Your Want Box

The hard thing about the Want Box is that you want a bunch of different things—or, rather, there are a bunch of different sides of you, and each of them wants—and fears—its own stuff. And since some motivations have conflicting interests with others, you cannot, by definition, have everything you want. Going for one thing you want means, by definition, not going for others, and sometimes, it’ll specifically mean going directly against others. The Want Box is a game of compromise.

The Yearning Octopus

To do a proper Want Box audit, you need to think about what you yearn for in a career and then unpack the shit out of it. Luckily, we have someone here who can help us. The Yearning Octopus.

We each have our own personal Yearning Octopus5 in our heads. The particulars of each person’s Yearning Octopus will vary, but people also aren’t all that different from each other, and I bet many of us feel very similar yearnings and fears (especially given that I find that Wait But Why readers tend to have a lot in common).

The first thing to think about is that there are totally distinct yearning worlds—each living on one tentacle. These tentacles often do not get along with each other.

It gets worse. Each tentacle is made up of a bunch of different individual yearnings and their accompanying fears—and these often massively conflict with each other too.

Let’s take a closer look at each tentacle to see what’s going on.

The Personal Yearnings tentacle is probably the hardest one to generalize here—it’s pretty particular to each of us. It’s a reflection of our specific personality and our values, and it bears the burden of probably the most complex and challenging human need: fulfillment. It’s also in the shit dealing with not only our current selves, but a bunch of our past selves too. The dreams of 7-year-old you and the idealized identity of 12-year-old you and the secret hopes of 17-year-old you and the evolving passions of your current self are all somewhere on the personal tentacle, each throwing their own little fit about getting what they want, and each fully ready to make you feel horrible about yourself with their disappointment and disgust if you fail them. On top of that, your fear of death sometimes emerges on the personal tentacle, all needy about you leaving your mark and achieving greatness and all that. The personal tentacle is why you don’t find very many billionaires content to spend the rest of their life sipping cocktails on the beach—it’s a highly needy tentacle.

And yet, the personal tentacle is also one that often ends up somewhat neglected. Because in many cases, it’s the ickiest set of yearnings to really go for; because the fears of this tentacle aren’t scary in an immediate way—they creep in out of the background over time; and because the personal tentacle is always at risk of getting bowled over early in your career by the powerful animal emotions of the other tentacles. This neglect can leave a person with major regrets later on once the dust settles. An unfulfilled Personal Yearnings tentacle is often the explanation, for example, behind a very successful, very unhappy person—who may believe they got successful in the wrong field.

The Social Yearnings tentacle is probably our most primitive, animal side, with its core drive stemming back to our tribal evolutionary past. On the tentacle are a number of odd creatures.

As we’ve discussed before on this blog, we all have a Social Survival Mammoth living in our heads who’s earth-shatteringly obsessed with what other people think of us. This means he craves acceptance and inclusion and being well-liked, while likewise being petrified of embarrassment, negative judgment, and disapproval. He really really really wants to be in the in-group and he really really really doesn’t want to be in the outgroup. He’s quite cute though.

Then there’s your ego, who’s a similar character but even more needy. Your ego doesn’t just want to be accepted; it wants to be admired, desired, and fawned upon—ideally, on a mass scale. More upsetting to it than being disliked is being ignored. It wants to be relevant and important and widely known.

There are other characters milling about as well. Somewhere else on the social tentacle is a little judge with a little gavel who gets very butthurt if it thinks people aren’t judging you fairly—if you’re not appropriately appreciated. It’s very important to the judge that people are aware of exactly how smart and talented you think you are. The judge is also big on holding grudges—which is the reason a lot of people are driven more than anything by a desire to show that person or those people who never believed in them.

Finally, some of us may find a loving little dog on our social tentacle who wants more than anything in the world to please its owner, and who just cannot bear the thought of disappointing them. The one problem with this adorable creature is that its owner isn’t you. It’s a person with so much psychological power over you that, if you’re not careful, you may dedicate your whole career to trying to please them and make them proud. (It’s probably a parent.)

The Lifestyle Yearnings tentacle mostly just wants Tuesday to be a good day. But like, a really pleasant, enjoyable day—with plenty of free time and self-care and relaxation and luxuries.

It’s also concerned with your life in the big picture being as great as possible—as far as your lifestyle tentacle is concerned, you should be able to do what you want to do in life, when and how you want to do it, with the people you like most. Life should be full of fun times and rich experiences, but it should also roll by smoothly, without too much hard work and as few bumps in the road as possible.

The issue is, even if you place a high priority on your lifestyle yearnings, it’s pretty difficult to keep the whole tentacle happy at the same time. The part of the tentacle that just wants to sit around and relax will hold you back from sweating to build the kind of career that offers long-term flexibility and the kind of wealth that can make life luxurious and cushy and full of toys. The part of the tentacle that only feels comfortable when the future feels predictable will reject the exact kinds of paths that may generate the long-term freedom another part of the tentacle longs for. The side of you that wants a stress-free life doesn’t get along very well with the side of you that thirsts to be hang gliding off a cliff in Namibia like Richard Branson.

The Moral Yearnings tentacle thinks the rest of the tentacles of your Yearning Octopus are a real pack of dicks—each one more self-involved and self-indulgent than the next. The parts of you on the moral tentacle look around and see a big world that needs so much fixing; they see billions of people no less worthy than you of a good life who just happened to be born into inferior circumstances; they see an uncertain future ahead that hangs in the balance between utopia and dystopia for life on Earth—a future we can actually push in the right direction if we could only get our other tentacles out of our way. While the other tentacles fantasize about what you would do with your life if you had a billion dollars in the bank, the moral tentacle fantasizes about the kind of impact you could make if you had a billion dollars to deploy.

Needless to say, the other tentacles of your Yearning Octopus find the moral tentacle to be insufferable. They also can’t begin to understand philanthropy for philanthropy’s sake—they think, “Other people aren’t me, so why would I spend my time and energy working to help them?”—but they can understand philanthropy for their own motive’s sake. While the moral and lifestyle tentacles tend to be in direct conflict, others may sometimes find common ground—the social tentacle can get very into philanthropy if it’ll happen to win you respect and admiration from a highly regarded social group, and some people’s personal tentacle may find the meaning or self-worth it so craves in a philanthropic endeavor.

That’s why, when you do something philanthropic—or anything altruistic, really—there are a few separate things going on in your head. The part of you determined to get proper public credit for the deed lives on your social tentacle; the part of you that thinks “God I’m a good person” lives on your personal tentacle; and the part of you that really loves seeing the person or group you helped be better off lives on your moral tentacle. Likewise, not doing anything for others can hurt you on multiple tentacles—the moral tentacle because it feels guilty and sad, the social tentacle because this may cause others to judge you as a selfish or greedy person, and the personal tentacle because it may lower your self-esteem.

Your Practical Yearnings tentacle thinks all of this is fine and great—but it would also like to point out that it’s March 31st and your rent is due tomorrow, and the funny thing about that is that it logged into your bank account and saw that the number of dollars in it is actually less than the number of dollars that your landlord will need from you sometime in the next 34 hours. And yeah it knows that you deposited that check on Thursday and that it’s supposed to clear tomorrow morning, but your practical tentacle also could have sworn that just last month, all the tentacles promised that they’d make some sacrifices in order to build up at least a little bank account cushion so that simply paying the rent wouldn’t have to be really fucking stressful every month. Your practical tentacle also can’t help but notice that your social tentacle offered to buy a round of drinks for all nine people you went to the bar with last Saturday so those people would think of you as a classy, generous person, and that your lifestyle tentacle chose to rent what sure seems like a pretty nice-ass apartment for someone now living check to check, and that the updates have gotten real quiet from your friend about that bagel delivery service he started six months ago that your moral tentacle happily invested $2,500 in to help it get off the ground, and oh also that meanwhile your personal tentacle has everyone sweating their dick off working at two comedy-writing internships simultaneously that somehow manage to bring in less money combined than you made dressing up as an Egyptian enchantress to wait tables at Jekyll & Hyde sophomore year of college.

At its basic level, your practical tentacle wants to make sure you can eat food and wear clothes and buy the medicine you need and not live outside. It doesn’t really care how these things happen—it just wants them to happen. But then everyone else on the octopus makes your practical tentacle’s life super hard by being fucky about things. Every time your income goes up, your lifestyle tentacle decides to raise the bar on what it wants and expects, leaving your practical tentacle continually in the shit trying to cover it all so you don’t have to run up your credit card debt. Your personal tentacle has all of these weird needs that take up a lot of time and more often than not aren’t exactly big money-makers. And while your practical tentacle would be totally down to just ask your rich uncle for money to help out, your social tentacle outlawed asking others for money because “it’s not a good look,” with your personal tentacle chiming in that “yeah, we’re better than that.”

So that’s the situation. You’ve got this Yearning Octopus in your head with five tentacles (or however many yours has), each with their own agenda, that often conflict with each other. Then there are the distinct individual yearnings on each tentacle, often in conflict amongst themselves. And if that weren’t enough, you sometimes have furious internal conflict inside a single yearning. Like when your desire to pursue your passion can’t figure out what it’s most passionate about.

Or when you want so badly to be respected, but then you remember that a career that wins the undying respect of one segment of society will always receive shrugs from other segments and even contemptuous eye rolls from other segments still.

Or when you decide to satisfy your urge to help others, before realizing that the part of you that wants to dedicate your life to helping to mitigate humanity’s greatest existential risks has palpable disdain for the part of you that would rather make a tangible positive impact on your local community—while the part of you that can’t stand the thought of the millions of today’s humans without access to clean water finds both of those other yearnings to be pretty cold and heartless.

So yeah, your Yearning Octopus is complicated. And no human in history has ever satisfied their entire octopus—that’s why you’ll never find it fully smiling. Human yearning is a game of choices and sacrifices and compromise.

Dissecting the Octopus

With that in mind, let’s return to your Want Box. When we think about our career goals and fears and hopes and dreams, our consciousness is just accessing the net output of the Yearning Octopus—which is usually made up of its loudest voices. Only by digging into our mind’s subconscious can we see what’s really going on.6

The cool thing is that we all have the ability to do that. The stuff in your subconscious is like stuff in the basement of a house. It’s not off-limits to us—it’s just in the basement. We can go look at it anytime—we just have to A) remember that the house has a basement, and B) actually spend the time and energy to go down there, even though going down there might suck.

So let’s head to the basement of your mind to look for the octopus. Unless you’re one of those people who’s really practiced at analyzing your subconscious, it might be dark in the basement, making it hard to see your octopus. The way to start turning the lights on is by identifying what your conscious mind currently knows about your yearnings and fears, and then unpacking it.

Like if there’s a certain career path that sounds fantastic to you, unpack that. Which tentacles in particular are yearning for that career—and which specific parts of those tentacles?

If you’re not currently working towards that career you supposedly yearn for, try to figure out why not. If you think it’s because you’re afraid of failing, unpack that. Fear of failure can emerge from any of the tentacles, so that’s not a specific enough analysis. You want to find the specific source of the fear. Is it a social tentacle fear of embarrassment, or of being judged by others as not that smart, or of appearing to be not that successful to your romantic interests? Is it a personal tentacle fear of damaging your own self-image—of confirming a suspicion about yourself that haunts you? Is it a lifestyle tentacle fear of having to downgrade your living situation, or of bringing stress and instability into a currently predictable life? Or maybe that fear of a living situation downgrade isn’t actually emerging from your lifestyle tentacle, but more so from your social tentacle—in other words, is it possible you’re indifferent about the apartment change itself but super concerned about the message a lifestyle downgrade sends to your friends and family? Or are there financial commitments you simply cannot back out of at the moment, and your practical tentacle is in a genuine panic about how you’ll make ends meet should this career switch take longer than expected to work out, or not work out at all? Or are a few of these combining together to generate your fear of making the leap?

Perhaps you don’t really think it’s fear of failure that’s stopping you, but something else. Maybe it’s a dread of the change in identity—both internally and externally—that inevitably accompanies a career move like this. Maybe it’s the heavy weight of inertia—an intense resistance to change—that seems to exist in and of itself and overpowers all of your other yearnings. In either case, you’d want to unpack the feeling and ask yourself exactly which tentacles are so opposed to an identity shift, or so driven by inertia.

Maybe you pine to be rich. You fantasize about a life where you make $1.2 million a year, and you feel a tremendous drive to make it happen. All five tentacles can feel a desire for wealth under certain circumstances, each for their own reasons. Unpack it.

As you unpack an inner drive to make money, maybe you discover that at its core, the drive is more for a sense of security than for vast wealth. That can be unpacked too. A yearning for security at its simplest is just your practical tentacle doing what your practical tentacle does. But maybe it’s not actually basic security you want as much as a guarantee of a certain level of fanciness demanded by your lifestyle or social tentacle. Or perhaps what you really want is a level of security so over-the-top secure it can no longer be called a security yearning—instead, it may be an impulse by the emotional well-being section of your lifestyle tentacle to alleviate a compulsive financial stress you were raised to forever feel, almost regardless of your actual financial situation.

The answers to all of these questions lie somewhere on the tentacles of your Yearning Octopus. And by asking questions like these and digging deep enough to identify the true roots of your various yearnings, you start to turn on the basement light and acquaint yourself with your octopus in all its complexity.

You’ll also come to understand which of your inner yearnings seem to speak the loudest in your mind and carry the most pull in your decision-making processes. Pretty quickly, a yearning hierarchy will begin to reveal itself. You’ll identify yearnings that speak loudly and get their way; yearnings that cry at the top of their lungs but get continually elbowed out of the way by higher-prioritized parts of the octopus; yearnings that seem resigned to their low-status positions in the hierarchy.

Searching for Imposters

We’re making good progress—but we’re just getting started. Once you have a reasonably clear picture of your Yearning Octopus, you can start doing the real work—work that takes place another level down in your subconscious, in the basement of the basement. Here, you can set up a little interrogation room and one by one, bring each yearning down into it for a cross-examination.

You’ll start by asking each yearning: how did you end up here, and why are you the way you are? Desires, beliefs, values, and fears don’t materialize out of nowhere. They’re either developed over time by our internal consciousness as observations and life experience pour in, or they’re implanted in us from the outside, by someone else. In other words, they’re the product of either you the chef or you the cook.

So the goal here in your creepy interrogation room is to tug on the faces of each of your yearnings to find out if it’s authentically you, or if it’s someone else disguised as you.

You can pull on a yearning’s face by playing the Why Game. You’ll ask your initial Why—Why is this something I want?—and get to some kind of Because. Then you’ll keep going. Why did that particular Because lead you to want what you now want? And when did that particular Because gain so much gravity with you? You’ll get to a deeper Because behind the Because. And if you continue with this, you’ll usually discover one of three things:

1) You’ll trace the Why back to its origin and reveal a long chain of authentic evolution that developed through deep independent thought. You’ll pull on their face and confirm that the skin is real.

2) You’ll trace the Why back to an original Because that someone else installed in you—I guess the only reason I actually have this value is because my mom kind of forced it on me—and you realize that you never really thought to consider whether you actually independently agree with it. You never stopped to ask yourself whether your own accumulated wisdom actually justifies the level of conviction you feel about that core belief. In a case like this, the yearning is revealed to be an imposter pretending to be an authentic yearning of yours. You pull on its face and it’s a mask that comes off, exposing the yearning’s original installer underneath.

3) You’ll trace the Why back and back and get kind of lost in a haze of “I guess I just know this because it’s true!” This could be an authentic you thing, or just another version of #2, in an instance where you can’t recall the moment this feeling was installed in you. Somewhere deep in you, you’ll have a hunch about which it is.

In a #1 scenario, you can be proud that you developed that part of you like a chef. It’s an authentic and hard-earned feeling or value.

In a #2 or maybe #3 scenario, you’ve discovered that you’ve been duped. You’ve let someone else sneak onto your Yearning Octopus while you weren’t looking. When it comes to that particular belief of yours, you’re a cook following someone else’s recipe—an obedient robot reciting desires and fears out of someone else’s brain.

There’s a chance you’re an unusually wise person whose examination reveals an octopus developed mostly by you and kept readily up to date. More likely, you’re like me and most of my friends—your interrogation room reveals some definite imposters, or at least a lot of ambiguity. Like, underneath one mask, you’ll find your mom.

You’ll pull off others to reveal the values and judgments of broader conventional wisdom, or the viewpoints of your more immediate community, or what’s considered cool by the dominant culture of your generation or the immediate culture within your closest group of friends.

Sometimes you’ll get to the end of a Why-Because pathway only to find the philosophy in a famous novel, or something a celebrity hero of yours once said in an interview, or a strong opinion one of your professors always repeated.

You might even find that some of your yearnings and fears were written by you…when you were seven years old. Like a childhood dream that was etched into the back of your consciousness as the thing you believe you really want, when you’re being truly honest.

The interrogation room probably won’t be that fun a time. But it’s time well spent—because you’re not your 7-year-old self, just like you’re not your parents or your friends or your generation or your society or your heroes or your past decisions or your recent circumstances. You’re Current-Age You—the only person, and the only version of yourself, who is actually qualified to want and not want the things you want and don’t want.

To be clear, this isn’t to say that it’s wrong to live by the words of a wise parent or a famous philosopher or friends you respect or the convictions of a younger you. Humble people are by definition influence-able—influences are an important and inevitable part of who each of us is. The key distinction is this:

Do you treat the words of your external influences as information, held and considered by an authentic inner you, that you’ve carefully decided to embrace? Or are your influences themselves actually in your brain, masquerading as inner you?

Do you want the same thing someone else you know wants because you heard them talk about it, you thought about it alongside your own life experience, and you eventually decided that, for now, you agree? Or because you heard someone talk about what they want or fear, and you thought, “I don’t know shit and that person does, so if they say X is true, I’m sure they’re right”—and then you etched those ideas into your mind, never again feeling the need to question them?

The former is what chefs do. The latter is what you do when you’re being an obedient robot. And a robot is what you become when at some point you get the idea in your head that someone else is more qualified to be you than you are.

The good news is that all humans make this mistake—and you can fix it. Just like your subconscious is right there for viewing if you want to view it—it’s also there for changing and updating and rewriting. It’s your head—you’re allowed to do with it what you want.

So it’s time for some evictions. Masked imposters have to go. Even mom and dad.

At the end of this, your octopus may look a little barren, leaving you feeling a little like you don’t know who you even are anymore. We usually think of this as a bad feeling, or even an existential crisis, but it actually means you’re doing better than most people.

The drop from naive over-confidence to wise, realistic humility never feels good, but pausing the roller coaster while it’s still on that first cliff and avoiding the pain—which turns out to be a lot of people’s move—isn’t a great strategy. Wisdom isn’t correlated with knowledge, it’s correlated with being in touch with reality—it’s not how far to the right you are on the graph, it’s how close you are to the orange line. Wisdom hurts at first, but it’s the only place where actual growth happens. The irony is that the cliff-pausers of the world like to make the wiser, braver valley-dwellers or continual-climbers feel bad about themselves—because they fundamentally don’t get how knowing yourself works. They haven’t reached that stage yet.

Getting to know your real self is super hard and never complete. But if you’ve tumbled off the cliff, you’ve gone through a key rite of passage and progress is now possible. As you climb up the orange line, you’ll slowly but surely begin to repopulate your Yearning Octopus with your real self.

At the moment, it probably won’t be obvious what those missing yearnings of yours are exactly—because they’re on an even deeper floor of your subconscious. They’re in the basement of the basement of the basement—in a place called Denial Prison.

Denial Prison

Our brain’s Denial Prison is a place most of us don’t even know is there—it’s where we put the parts of us we repress and deny.

The authentic yearnings of ours that we’re in touch with—i.e. those that proved to be authentic during interrogation—were easy parts of our true selves to find in our subconscious, lying in plain sight, right below the surface of our consciousness. Even our conscious mind knows these yearnings well, because they frequently make their way upstairs into our thoughts. These are the parts of us we have a healthy relationship with.

But then there are the parts of you that weren’t living on your octopus where they’re supposed to be—instead, you found an imposter in their place. These lost parts of you are often incredibly hard to access, because they’ve been living deep in your subconscious, on a floor so low it’s almost not there at all. Almost.

Some parts of us are banished down on basement #3 because they’re extraordinarily painful for us to acknowledge or think about. Sometimes new parts of us are born only to be immediately locked up in prison as part of a denial of our own evolution—i.e. out of stubbornness. But there are other times when a part of us is in Denial Prison because someone else locked it up down there. In the case of your yearnings, some of them will have been put there by whatever masked intruder had been taking its place. If dad has successfully convinced you that you care deeply about having a prestigious career, he probably has also convinced you that the part of you that, deep down, really wants to be a carpenter isn’t really you and isn’t what you really want. At some point during your childhood, he threw your passion for carpentry into a dark, dank Denial Prison cell.

So let’s gather your courage and head down to the basement of the basement of the basement of your mind and see what we find.

You may pass some unpleasant characters.

Leave them for another time—right now, search for locked-away career-related yearnings. Maybe you’ll find a repressed passion to teach. Or a desire to be famous that your particular tribe has shamed you out of. Or a deep love of long blocks of free, open leisure time that your hornier, greedier teenage self kicked downstairs in favor of a raging ambition.

There will be certain parts of your authentic self you won’t be able to uncover in Denial Prison—it’s pretty dark down there. But be patient—now that you’ve done your audit and cleared space for them on your octopus, they may begin to emerge.

Priority Rankings

The other part of our Yearning Octopus audit will address the hierarchy of your yearnings. Almost as important as the yearnings themselves is the priority they’re given. The hierarchy is easy to see because it’s revealed in your actions. You may like to think a desire to do something bold is high up on your hierarchy, but if you’re not currently working on something bold, it reveals that however important boldness is to you, something else—some source of fear or inertia in you—is currently being prioritized above it.

It’s important to remember that a ranking of yearnings is also a ranking of fears. The octopus contains anything that could make you want or not want to pursue a certain career, and the reverse side of each yearning is its accompanying fear of the opposite. The reverse side of your yearning to be admired is a fear of embarrassment. If you flip over your desire for self-actualization, you’ll see a fear of underachieving. The other half of your craving of self-esteem is a fear of feeling shame. If your actions don’t seem to match what you believe is the internal hierarchy of your yearnings, usually it’s because you’re forgetting to think about the role your fears are playing. What looks like a determined drive for success, for example, might actually be someone running away from a negative self-image or trying to escape feelings like envy or under-appreciation. If your actions seem beholden to yearnings that you don’t believe you actually care that much about, you’re probably not looking closely enough at your fears.

With both yearnings and fears in mind, think about what your internal hierarchy might look like, and return that same important question: “Who made this order? Was it really me?”

For example, we’re often told to “follow our passion”—this is society saying “put your passion yearnings at the top of your hierarchy.” That’s a very specific instruction. Maybe that’s the right thing for you, but it also very well might not be. It’s something you need to independently evaluate.

To get this right, let’s try to do a fresh ranking, from first principles, based on who we really are, how we’ve evolved over time, and what really matters to us most, right now.

This isn’t about which yearnings or fears have the loudest voices or which fears are most palpable—if it were, you’d be letting your impulses take the wheel of your life. The person doing the ranking is you—the little center of consciousness reading this post who can observe your octopus and look at it objectively. This involves another kind of compromise. On one side, you’ll try to tap into all the wisdom you’ve accumulated throughout your life and make active decisions about values—about what you really believe is important. On the other side, it’s about self-acceptance and self-compassion. Sometimes you’ll have strong undeniable yearnings that you’re not super proud of—whether you like it or not, those are part of you, and when you neglect them, they may cause a continual stink and make you miserable. Creating your yearning hierarchy is a give and take between what’s important and what’s you. It’s probably a good goal to give higher priority to your more noble qualities, but it’s okay to throw a bone to some of your not-so-noble sides as well—depending on where you decide to draw the line. There’s a wisdom to knowing when to accept your not-so-noble side and when to reject it entirely.

To get all of this in order, we want a good system. You can play around with what works for you—I like the idea of a shelf:

This divides things into five categories. The absolutely highest priority inner drives get to go in the extra special non-negotiable bowl. The NN bowl is for yearnings so important to you that you want to essentially guarantee that they’ll happen—at the expense of all other yearnings, if necessary. This is why so many of history’s legends were famously single-minded—they had a very intense NN bowl yearning and it led them to world fame, often at the expense of relationships, balance, and health. The bowl is small because it should be used very sparingly—if at all. Like maybe only one thing gets it. Or maybe two or three. Too many things in the NN bowl cancels out its power, making that the same as having nothing in the bowl at all.

Your group of top shelf yearnings is mostly what will drive your career choices—but top shelf placement should also be doled out sparingly (that’s why it’s not a very large shelf). Shelf placement is as much about de-prioritizing as it is about prioritizing. You’re not just choosing which parts of you are the most important to make you happy, you’re choosing which parts of you to intentionally leave wanting or even directly opposed. No matter what your hierarchy looks like, some yearnings will be left feeling very unhappy and some fears will feel like they’re being continually assaulted. This is inevitable.

That’s why most yearnings should be on the middle shelf, the bottom shelf, or the trash can. The middle shelf is good for those not-so-noble qualities in you that you decide to accept. They deserve some of your attention. And they’ll often demand it—core parts of you won’t go quietly into non-prioritization, and they sometimes can really ruin your life if they’re neglected.

Most of the rest will end up on the bottom shelf. Putting a part of you on the bottom shelf is telling it, “I know you want these things, but for now, I’ve decided other things are more important. I promise to revisit you a little later, after I’ve gotten some more information, and if I change my mind, you’ll get a shelf upgrade then.” The best way to think of the bottom shelf is this: the more yearnings you can convince to accept a bottom shelf rating, the better the chances your top shelf and NN bowl yearnings have of getting what they want. Likewise, the fewer yearnings you put on the top shelf, the more likely those on the top shelf will be to thrive. Your time and energy are severely limited, so this is a zero-sum compromise. The amateur mistake is to be too liberal with the NN bowl and top shelf and too sparing with the large bottom shelf.

Then there’s the trash can, for the drives and fears you flat-out reject—those parts of you that fundamentally violate the person your wisest self wants to be. A good amount of inner conflict emerges from people’s trash cans, and trash can control is a major component of integrity and inner strength. But like the rest of your hierarchy decisions, your criteria for what qualifies as trash should be derived from your own deep thought, not from what others tell you is and is not trash.

As you go through this difficult prioritizing process—inevitably, at times, against the screaming protests of unhappily deprioritized yearnings—remember that you’re the only wise one in the room. Yearnings and fears are impatient and bad at seeing the big picture. Even a seemingly high-minded yearning, like those on the moral tentacle, can’t understand the complete picture in the way you can. Many of the people who have done wonders to make the world better got there on a path that started with selfish motives like wealth or personal fulfillment—motives their moral tentacle probably hated at first. The octopus won’t be the wise adult in the room—that’s your job.

Finally, as we’ll discuss more later, this is not a permanent decision. It’s the opposite—it’s a rough draft written in light pencil. It’s a hypothesis that you’ll be able to test and then revise based on how actually living this hierarchy feels in practice.

Your Want Box is ready to go. Now let’s turn to your Reality Box.

Deep Analysis, Part 2: Your Reality Box

The Want Box deals with what you find desirable. The Reality Box deals with what’s possible.

But when we examined the Want Box, it became clear that it’s not necessarily based on what you actually want—it’s based on what you think you want—what you’re in the habit of wanting.

The Reality Box is the same deal. It doesn’t show you reality, it shows your best crack at what reality might be—your perception of reality.

The goal of self-reflection is to bring both of these boxes as close to accuracy as possible. We want our perceived yearnings to be a true reflection of our authentic inner selves, and we want our beliefs about what’s possible to come close to mirroring what’s actually possible. For our Want Box audit, we looked under the hood of the Want Box and found its settings—your yearnings and fears. When we open the hood of your Reality Box, we see a group of beliefs.

When it comes to your career possibilities, you’re dealing with two sets of beliefs: beliefs about the world and beliefs about your own potential. For a career option to qualify for your Reality Box, your potential in that career area has to measure up to the objective difficulty of achieving success in that area.

Us being us, we’re probably pretty bad at assessing either side of this comparison accurately.

I don’t know how you think about career path difficulty, but in my experience, people often see it like this:

There are traditional careers—stuff like medicine or law or teaching or a corporate ladder, etc.—and these careers have predictable, set paths. If you’re decently smart and work hard, you’ll end up in a successful, stable situation.

Then there are less traditional careers—the arts, entrepreneurship, non-profit work, politics, etc.—and these are wildcards. Success and stability are no guarantee, and to reach great heights, it’s either a lottery ticket game of luck, a genetic lottery game of innate talent, or some combination of the two.

These are perfectly reasonable assumptions—if you live in 1952. Your beliefs about the world of careers and about what it takes to succeed need just as thorough an unmasking as your yearnings did—and I suspect that behind most of them, you’ll find big, fat conventional wisdom. You might first pull off the mask of one of your beliefs and find your parents or your friends or your college career coach—but if you keep going and pull on their face, you’ll usually see that it’s also a mask, and conventional wisdom is there hiding behind it. A general conception, a common opinion, an oft-cited statistic7—none of which have actually been verified by you, but all of which are treated as gospel by society.

Today’s world goes through dramatic changes each decade, which usually leaves conventional wisdom wildly outdated. But we’re wired for a more ancient world where almost nothing ever changed, so we all reason like cooks and treat conventional wisdom as equivalent to truth.

These problems then extend to how we view our own potential. When you overrate the impact of innate talent on how people fare in their careers—and you also conflate talent and skill level—it won’t leave you feeling great about your chances at many paths. Because we better understand the trajectory of traditional careers, we’re less prone to do this with them. A first-year medical student sees an experienced surgeon at work and thinks, “I can get there one day—just need to do about 20 years of hard work.” But when a young artist or entrepreneur or software engineer looks at the equivalent of the experienced surgeon in their field, they’re more likely to think, “Wow look how talented they are—I’m nowhere near that good,” and get all hopeless. There’s also the other common notion, that people who thrive in non-traditional careers had some “big break” at some point, like hitting a lucky scratch card jackpot—and I don’t know many people who want to risk their careers on scratch cards.

These are only a few examples of the slew of delusions and misconceptions we tend to have about how great careers happen. So let’s brainstorm how it might actually work:

The Career Landscape

I have no idea, mostly. And I think most people have no idea. Things are just changing too quickly.

But that’s kind of the key point. If you can figure out how to get a reasonably accurate picture of the real career landscape out there, you have a massive edge over everyone else, most of whom will be using conventional wisdom as their instruction booklet.

First, there’s the broad landscape—the set of all the jobs someone could possibly have in today’s society. My current job description is: “Writer of 8,000-to-40,000-word articles about a bunch of different topics, with cursing and stick figures, on a remarkably sporadic schedule.” Think conventional wisdom has any job openings for me with that description? The landscape today is made up of thousands of options—some 40 years old, some made possible only three months ago because of the advent of some new technology—and the way things work today, if there’s an option you want that’s not already out there, you can probably create it for yourself. Pretty stressful, but also incredibly exciting.

Then, there’s each specific career path. A career path is like a game board. The conventional wisdom bookshelf contains instruction booklets for only a small fraction of today’s available game boards—and those that it does have usually tell you how that game was played in the past, even though the current game board has evolved significantly into something with new kinds of opportunities and different rules and loopholes. When you consider a career path today, to make an accurate assessment of what the path looks like and what kinds of strength-weakness profiles it favors, you have to understand what that career’s current game board looks like. Otherwise, it’s like trying to evaluate your chances of being a professional basketball player based on your height and strength without realizing that, say, basketball has evolved and is now played on oversize courts that contain 10 different 7-foot hoops, and the current game favors speed over height and strength.

This is promising news. There are likely dozens of awesome career paths that beautifully match your natural strengths, and it’s likely that most other people trying to succeed on those paths are playing with an outdated rulebook and strategy guide. If you simply understand what the game board really looks like and play by modern rules, you have a huge advantage.

Your Potential

And this brings us to you and your particular strengths. Not only do we assess our strengths based on the wrong game boards (like in our basketball example)—even when we have the right game board in mind, we’re often bad at identifying the real strengths that that game calls for.

When assessing your chances on a certain career path, the key question is:

With enough time, could you get good enough at this game to potentially reach whatever your definition of success is in that career?

I like to view this journey to “good enough at the game to succeed” as a distance. The distance starts with where you are now—point A—and ends with you reaching your definition of success, which we can draw with a star.

The length of the distance depends on where point A is (how far along you are at the current moment) and where the star is (how lofty your definition of success is).

So if you’re a college graduate who majored in computer science and your career goal is to be a middle-of-the-ladder engineer at Google, your distance might look like this:

But if you’ve never done any kind of computer science before, and your career goal is to be the top engineer at Google, you’ve got a much longer road ahead:

If your goal is to create the new Google, the road gets much, much longer.

At this point, conventional wisdom might emerge as a voice in your head and point out that simply getting good enough at a certain skill doesn’t actually guarantee success—you might reach the star on a career path and still find that you haven’t “made it” yet.

That’s mostly wrong, because it’s misunderstanding the star. The star isn’t about a particular skill level—e.g. coding ability or acting skills or business savvy—it’s about the entire game. In traditional careers, the games tend to be more straightforward—if you want to be a top surgeon, and you get incredibly good at surgery, you’ve probably hit your star and you’ll have your career. But the game boards in less traditional careers often involve many more factors. Reaching the “I want to be a famous actor” star doesn’t simply mean getting as good at acting as Morgan Freeman, it means getting as good at the entire actor game as most movie stars get by the time they break through. Acting ability is only one piece of that puzzle—you also need a knack for getting yourself in front of people with power, a shrewdness for personal branding, an insane amount of optimism, a ridiculous amount of hustle and persistence, etc. If you get good enough at that whole game—every component of it—your chances of becoming an A-list movie star are actually pretty high. That’s what hitting the star means.

But conventional wisdom doesn’t get how non-traditional careers work—it only thinks in terms of a narrow aspect of success: talent and hard work. When career paths have game boards with much more going on, conventional wisdom just throws its hands up and calls it “luck.” To conventional wisdom, becoming a movie star requires some talent, but mostly, hitting a rare scratch ticket jackpot.

So how do you figure out your chances of getting to any particular star? It’s all about a simple formula:

Distance = Speed x Time.

In our case, the more apt wording might be:

Progress = Pace x Persistence.

Your outlook on any career quest depends on A) the pace at which you’ll be able to improve at playing that career’s “game” and B) the amount of time you’re willing to persist in chasing that star. Let’s talk about both of these:

Pace

What makes someone slower or faster at improving at a career game? I’d say it comes down to three factors:

Your level of chefness. As we discussed earlier, chefs look at the world with fresh eyes and build conclusions based on what they observe and what they’ve experienced. Cooks arrive at conclusions by following someone else’s recipe—in the case of careers, the recipe is usually conventional wisdom. Careers are complex games that almost everyone starts off bad at—then the chefs improve rapidly through a continual loop…

…while cooks improve at a snail’s pace, because their strategy is just following a recipe which itself barely changes. What’s more, in a world where career games are constantly evolving and morphing, the chef’s tactics can evolve in real time and keep up. Meanwhile, the cook’s recipe just grows more and more outdated—a problem they remain oblivious to. This is why I’m pretty convinced that at least for less traditional careers, your level of chefness is the single most important factor in determining your pace of improvement.

Your work ethic. This one is obvious. Someone who works on their career 60 hours a week, 50 weeks a year, is going to move down the path almost four times faster than someone who works 20 hours a week, 40 weeks a year. Someone who chooses a balanced lifestyle will move slower than a single-minded workaholic. Someone with a propensity towards laziness or procrastination is going to lose a lot of ground to someone who’s good at putting in consistent work days. Someone who frequently breaks from work to daydream or pick up their phone is going to get less done in each work hour than someone who practices deep focus.

Your natural abilities. Talent does matter. Smarter, more talented people will improve at a game at a faster rate than less naturally gifted people. But intelligence and talent are only two types of natural ability that come into play here. Cleverness and savvy matter too, and those qualities don’t always correlate with raw intelligence. Depending on the type of career, social skills can be critically important as well. In many careers, likable (or subtly manipulative) people have a big advantage over less likable people—and those who enjoy socializing will put in more people hours over time, and build deeper relationships, than antisocial types.

Other things, like existing connections, existing resources, and existing skills matter, of course, but they’re not components of pace—they’re part of the location of point A.

Persistence

When I say persistence, I’m referring to long-term persistence (as opposed to day-to-day work ethic). Persistence is simpler than pace. The more years you’re willing to commit to chasing a star, the farther along the road towards the star you’ll get. A car going 30 mph that quits driving after 15 minutes gets a lot less far than a car that drives 10 mph for two hours.

And this is why persistence is so important. Someone who has decided they’re only willing to give a dream career a shot for three years before they’ll go for their fallback plan has essentially disqualified themselves from a chance at their dreams. It doesn’t matter how awesome you are—if you’ll give up after two or three years of not breaking through, you’re unlikely to succeed. A few years is just not enough time to traverse the typically long distances it takes to get to the raddest success stars, no matter how impressive your pace.

Your Real Strengths and Weaknesses

With our pace-times-persistence equation in mind, let’s revisit the concept of strengths and weaknesses. It’s not that “strengths and weaknesses” is a bad concept—it’s that we think about it all wrong. When we list our strengths, we tend to list our areas of existing skill more than anything else. Instead, strengths should be all about pace and persistence qualities. Originality or lack thereof should be a critical component of the discussion, making qualities like agility and humility (trademark chef traits) notable strengths, and qualities like stubbornness8 or intellectual laziness (classic cook traits) important weaknesses. The subtleties of work ethic, like a knack for deep focus or a propensity to procrastinate, should also be a major part of the discussion, as should natural abilities beyond talent, like savvy and likability. Qualities related to persistence, like resilience and determination and patience, should be thought of as promising strengths, while a social tentacle clamoring to appear successful as quickly as possible should be viewed as a bright red flag.

Most importantly, these items shouldn’t be discussed as a snapshot of where they are now, but rather in terms of your potential for improvement in each of them. If you handed 25-year-old Michael Jordan a basketball for the first time, he’d suck. But calling basketball a “weakness” of his would be getting it very wrong. Instead, you’d want to watch him practice over the next six weeks and evaluate the slope of his improvement. This lesson applies to specific skills—but most general pace and persistence qualities can also be worked on and improved if you focus on them.

Filling in the Reality Box

Your true Reality Box would literally include all career paths for which you think a highly improved version of yourself could, with an entire lifetime of effort, reach the minimum star you’d be comfortable defining as success. This would be an impossibly big list, only ruling out paths that are clearly far too long for you to traverse at your maximum possible pace on the path (like me chasing a career as an Olympic figure skater). But it’s still useful to pause for a minute and reflect on the vast extent of your full Reality Box—just acknowledging how many options are truly open to you can put you in the right mindset.9

So to be a bit more efficient, let’s worry about the parts of the Reality Box that might actually end up in your Option Pool (the middle of the Venn diagram where the Want and Reality Boxes overlap). To complete our Reality Box audit with that caveat, we need to evaluate:

1) The general landscape. Take our best crack at evaluating the world’s current career landscape—the full range of options available (or create-able).

2) Specific game boards. For any careers that sound remotely interesting, ponder what the deal might be with that career’s current game board—the parties involved, the way success seems to be happening for others recently, the most up-to-date rules of the game, the latest new loopholes that are being exploited, etc.

3) Starting point. For those paths, evaluate your starting point, based on your current skills, resources, and connections relevant to that field.

4) Success point. Think about end points and where on each line your star should be placed. Ask yourself what’s the minimum level of success you’d need to achieve in order to feel happy about having chosen that career path.

5) Your pace. Make an initial estimate for what your pace of improvement might be on these various game boards, based on your current pace-related strengths and how much you think you can improve at each of them (in other words, how much your speed might be able to accelerate).

6) Your level of persistence. Evaluate the amount of time you think you’ll be willing to put into each of these respective paths.

Now it’s just math. You take your game board and make it a line, you plot starting points and success stars that together generate the various distances in front of you, and for each, you multiply your pace by your level of persistence. If it seems like the product of your pace and persistence for a given career path might be able to measure up to the path’s total length, that career lands in your Reality Box. Of course, it’s impossible to get exact values for any of the above factors, but it’s good to at least know the equation you’re working with.

A from-first-principles Reality Box audit may bring some overly optimistic people down to Earth, but I suspect that for most, an audit will leave them feeling like they have a lot more options than they realized, empowering them to set their sights on a bolder direction.

A good Reality Box reflection warrants yet another Want Box reflection. Reframing a bunch of career paths in your mind will affect your level of yearning for some of them. One career may seem less appealing after reminding yourself that it will entail thousands of hours of networking or multiple decades of pre-success struggle. Another may seem less daunting after changing your mind about how much luck is actually involved. There will be other career paths you hadn’t considered wanting because you hadn’t considered them as real options, but some deep reflection has opened your mind to them.

This brings us to the end of our long, two-part deep dive. After a fairly exhausting box-auditing process, we can return to our Venn10 diagram.

Assuming some things have changed, you have a new Option Pool to look at—a new list of options on the table that seem both desirable to your high-priority rankings and possible to achieve. We’re ready now to return to where we were before we started our analysis: the present moment. With these options in front of us, we’re ready to lift our heads up out of analysis and look forward into the future.

Connecting the Dots into the Future

It’s time to bring back your Career Plans map that I made you put down at the beginning of the post—the one with the arrow or the question mark. If there had been a clear arrow on your map before your audit, check out your new Option Pool. Given everything you’ve reflected upon, does your current career plan still qualify to be there? If so, congrats—you’re ahead of most of us.

If not, well that’s shitty news, but it’s also good news. Remember, going from a false arrow to a question mark is always major progress in life.

And actually, a new question mark implies having made the key cliff jump on two roller coasters: getting to know yourself and getting to know the world. Major step in the right direction. Cross out the arrow and join the question mark crowd.

Now the question mark crowd has a tough choice. You gotta pick one of the arrows in the Option Pool.

It’s a tough choice—but it should be way less tough than it is. Here’s why:

Careers used to be kind of like a 40-year tunnel. You picked your tunnel, and once you were in, that was that. You worked in that profession for 40 years or so before the tunnel spit you out on the other side into your retirement.

The truth is, careers have probably never really functioned like 40-year-tunnels, they just seemed that way. At best, traditional careers of the past played out kind of like tunnels.

Today’s careers—especially the less traditional ones—are really really not like tunnels. But crusty old conventional wisdom has a lot of us still viewing things that way, which makes the already hard job of making big career path choices much harder.

When you think of your career as a tunnel, it causes an identity crisis in anyone who doesn’t feel sure of who exactly they are and who they’ll want to be decades from now—which is most sane people. It enhances the delusion that what we do for work is a synonym for who we are, making a question mark on your map seem like an existential disaster.

When you think of your career as a tunnel, the stakes to make the right choice seem so high that it explodes the feeling of tyranny of choice. For perfectionist types especially, this can be utterly paralyzing.

When you think of your career as a tunnel, you lose the courage to make a career switch, even when your soul is begging for it. It makes switching careers feel incredibly risky and embarrassing, and it suggests that someone who does so is a failure. It also makes all kinds of multi-faceted, vibrant, mid-career people feel like they’re too old to make a bold switch or start a whole new path afresh.

But conventional wisdom still tells many of us that careers are tunnels. As the icing on its shit cake—on top of helping us yearn for things we don’t actually want, deny yearnings that we feel deep down, fear things that aren’t dangerous, and believe things about the world and our potential that aren’t accurate—conventional wisdom tells us that careers are a tunnel to help us daunt the shit out of ourselves unnecessarily.

Today’s career landscape isn’t a lineup of tunnels, it’s a massive, impossibly complex, rapidly changing science laboratory. Today’s people aren’t synonymous with what they do—they’re impossibly complex, rapidly changing scientists. And today’s career isn’t a tunnel, or a box, or an identity label—it’s a long series of science experiments.

Steve Jobs compared life to connecting the dots, pointing out that while it’s easy to look at your past and see how the dots connected to lead you to where you are, it’s basically impossible in life to connect the dots forwards.

If you look at the biographies of your heroes, you’ll see that their paths look a lot more like a long series of connected dots than a straight and predictable tunnel. If you look at yourself and your friends, you’ll probably see the same trend—according to data, the median time a young person stays in a given job is only 3 years (older people spend a longer time on each dot, but not that much longer—10.4 years on average).

So seeing your career as a series of dots isn’t a mental trick to help you make decisions—it’s an accurate depiction of what’s actually happening. And seeing your career as a tunnel isn’t just unproductive—it’s delusional.

Likewise, you’re limited to focusing mainly on the next dot on your path—because it’s the only dot you can figure out. You don’t have to worry about dot #4 because you can’t anyway—you’re literally not qualified to do so.

By the time dot #4 rolls around, you will have learned stuff about yourself you don’t know now. You’ll also have changed from who you are now, and your Yearning Octopus will reflect those changes. You’ll know a lot more than you currently do about the career landscape and the specific game boards you’re interested in, and you’ll have become a much better game player. And of course, that landscape—and those game boards—will have themselves evolved.

Pretending you can figure out what dot #2 or #4 or #8 should be now is laughable. Future dots are the worry of a future, wiser you living in a future world. So let’s focus on dot #1.

If we’re thinking of ourselves as scientists and of society as a science lab, we should think of your current freshly revised Want-Reality Venn Diagram as nothing more than an early, rough hypothesis. Dot #1 is your chance to test it out.

Hypothesis testing is intuitive in the dating world. If a friend were toiling over what kind of person she wants to marry but never went out with anyone, you’d tell her, “You can’t figure this out on your couch—you’ve gotta start going on dates, and that’ll teach you what you want in a partner.” If that friend then went on a solid first date and returned home to toil for hours about whether or not this new person was The One, you’d again have to correct her. You’d say, “There’s no way you can know that from just one date! You have to get some experience dating this person to learn what you need to learn to make that decision.”

We can all agree that this hypothetical friend is pretty nuts and is lacking a fundamental understanding of how you find a happy relationship. So let’s not be like her when it comes to picking our career. Dot #1 is a chill situation—it’s just a first date.

This is awesome news—because it makes it a lot less scary to draw an arrow on your map if it’s only an arrow to dot #1 of your future. The real cause of tyranny of choice is accurately seeing the sheer number of options you have in today’s world while delusionally seeing those careers as the 40-year tunnels of yesterday’s world. That’s a lethal combo. Reframing your next major career decision as a far lower-stakes choice makes the number of options exciting, not stressful.

And that’s all great in theory. But now comes the hard part.

Making Your Move

You’ve reflected and reflected and reflected and weighed and measured and predicted and considered. You’ve chosen a dot and drawn an arrow. And now you have to actually make the move.

We’re super bad at this. We’re frightened people. We don’t like icky things and making a bold, real-life step is icky. If there’s any ounce of procrastination susceptibility in us, here’s where it’ll show itself.

The Yearning Octopus can help. As we discussed earlier, your behavior at any given point simply displays the configuration of your octopus. If you’ve decided on a life step and you can’t quite take it, it’s because the parts of you that don’t want to make a move are ranked higher in your subconscious than the parts of you that do. Your conscious mind may have tried to assign lower shelf ratings to the parts of your octopus that lean towards inertia, but your yearnings have rebelled. You’re a CEO not in control of their staff.

To fix this problem, think like a kindergarten teacher. In your class, a faction of the 5-year-olds is rebelling against your wishes. What do you do?

Go talk to the 5-year-olds that are causing the trouble. They’re unpleasant, defiant simpletons, but they can still be reasoned with. Talk to them about why you’ve ranked them lower than others in the octopus hierarchy. Describe to them the insights you gained from your Reality Box reflection. Remind them about how connecting the dots works and about the chillness of dot #1. You’re the teacher—figure it out.

The older I get, the clearer it becomes that our internal battle as the kindergarten teachers of our mind is like 97% of life’s struggle. The world is easy—you’re difficult. If you find yourself continually not executing your plans in life and your promises to yourself, you’ve uncovered your new #1 priority—becoming a better kindergarten teacher. Until you do, your life will be run by a bunch of primitive, short-sighted 5-year-olds, and your whole shit will suck. Trust me, I know.

If your inner analysis does call for a career leap to a new dot, I hope that at some point, you’re able to make the jump.

After the Move

Jumping to a new dot is a liberating feeling, usually side by side with some substantial internal havoc.

First of all, for a while at least, you’ll probably suck at what you’re doing on your new dot. While your wise self will know that’s exactly how it should be, your less wise selves will go into full existential meltdown mode. All of the fears you so thoughtfully deprioritized in your octopus ranking will think someone is murdering them and they’ll start trying to call 911. The yearnings you did prioritize won’t be feeling much gratification yet, and they’ll wonder if they were wrong all along about what they thought they wanted. The yearnings you didn’t prioritize will get out the guitar and start singing love songs for the greener-seeming grass you deprived them of. It won’t be much fun.

Even if things do go well, you’ll be quickly reminded of the fact that the Yearning Octopus is a generally unhappy creature. Core pieces of the octopus will feel neglected or even assaulted, and every day that goes by, you’ll be bearing the opportunity cost of the paths you were considering but chose not to walk down—the versions of you in parallel universes where you made other choices. You’ll think about their hypothetical advancement in the world and worry about what you may have passed up.

As you get wiser, you’ll learn to view a largely unhappy octopus with acceptance. You’ll let it whine and get good at tuning it out, knowing that it’s whining in the exact way you planned for it to be.

The whining octopus is a reminder of why pure, elated happiness is never a reasonable goal. The times you feel pure happiness are temporary, drug-induced delusions—like the honeymoon phase of a new relationship or new job or the high following a long-awaited success. Those moments are the perfect golf shots of a mediocre golfer’s outing—they’re awesome, and you should enjoy the shit out of them—but they’re not the new normal, and they never will be.

A better goal is contentment: the satisfying feeling that you’re currently taking the best crack you can at a good life path; that what you’re working on might prove to be a piece of an eventual puzzle you can feel really proud of. Chasing happiness is an amateur move. Feeling contentment in those times when your choices and your circumstances have combined to pull it off, and knowing you have all that you could ever ask for, is for the wise.

People talk about being present in the moment, but there’s also the broader concept of macro-presence: feeling broadly present in your own life. If you’re on a career dot that, when you’re being really honest with yourself, feels right, you get to stop thinking and stop planning for a while and just dig in. You’ll come back to the big picture later—for now, you can put the macro picture aside, put your head down, and dedicate all of your energy to the present. For a while, you can just live.

These moments don’t always last that long, so sink your teeth in. Put everything you’ve got into the dot you’ve chosen. As far as you know, you might be Michael Jordan holding his first basketball, so start playing.

The Next Dot?

At some point, your good feelings about the macro picture may sour. And when they do, you’ll have to get back into analysis mode and figure out what, in particular, is causing the restlessness.

Sometimes, the macro mission won’t be the problem. It’ll be that the chef in you has decided that the mission itself calls for a strategic dot jump. In these cases, jumping dots isn’t a release of persistence but the stuff of persistence. This is the mission-enhancing type of dot jump.

Other times, you’ll feel a darker kind of restlessness—the suspicion that you may need to change up the macro mission. When this happens, you’ll have to figure out if that feeling is emerging from the wise parts of you or simply from your restless, deprioritized yearnings. A mission-changing dot jump may be in order, but depending on which parts of you are asking for it, it may also be the wrong move.

In these moments, it’s important to consider where you tend to be on this spectrum:

The people on the left side of this spectrum are jump-shy. The cement-footed. Their pitfall is staying way too long in the wrong things. The people on the right are jump-happy—the wing-footed—and they have the opposite pitfall: they’re quick quitters.11 (You should be especially wary of cement feet—psychologists believe that people at the end of their lives are most likely to regret living by inertia: a commonly voiced regret is “I wish I had quit earlier,” and the most common advice of the elderly is, “Don’t stay in a job you dislike.“)

This is why these internal frameworks are important. They give you the ability to analyze the source of your impulses. In our example, the question is whether your impulse to jump missions is the result of genuine evolution or quick-quitter bias. So think about your diagram. Is your restlessness just the expected incessant whining of an octopus still correctly configured? The weariness from a long trudge on what’s still the right path for you? Or have you learned new information about yourself or the world during the trudge that has corrected some off-base initial assumptions? Or maybe something is fundamentally evolving—some blue or yellow loop activity:

If you feel that things have genuinely changed, you may decide to zoom out even further and think about the big red loop, which deals with fundamentally changing your mission:

If a career is like connecting the dots, we should probably rank “getting wise about dot-jumping” pretty high on our to-do list. The best place to start is by looking at your own past. Studying your own past decisions, with the flashlight of hindsight and accumulated wisdom, is like an athlete studying game tape.

Looking at my own past, I can see a lot of dot jumps (or, while I was still in school, career plan adjustments), and some of them look pretty unwise in retrospect. But the clearer a picture I can see of my past bad decisions and the thought patterns and behavioral habits that built them, the less likely I’ll be to repeat them in the future.

Remembering that you’re kind of dumb is also a critical humbling exercise. The insecurity of humility doesn’t feel very good, and the burden of having to continually invent your own life map is never easy—but insecurity and difficulty are the feelings of driving your own ship. It’s when we feel too good that we run the risk of becoming overconfident, intellectually complacent, and set in our ways. It’s exactly when we think we have life all figured out that we end up losing our way.

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Over the course of your life, your good and bad decisions will collaborate to forge your unique life path. Often on this blog, I’ve written about how irrational our fears can be and how badly they can hold us back. But we should probably embrace the fear of end-of-life regret.

I’ve thankfully never been on anything that felt like a deathbed, but it seems like there’s something about the end of life that lets people see things with clear eyes. It seems like facing death makes all of those voices in your head who aren’t actually you melt away, leaving your little authentic self standing there all alone, in reflection. I think end-of-life regrets may simply be your authentic self thinking about the parts of your life you never got to live—the parts of you that someone else kicked down into your subconscious.

My own psyche seems to back this up—looking back on my path so far, the mistakes that bother me most are the ones that happened because someone else took the wheel of my head and overruled the quiet, insecure voice of my authentic self—the mistakes that I knew at the time, deep down, were wrong. My goal for the future isn’t to avoid mistakes, it’s for the mistakes I do make to be my own.

That’s why I went through such an excruciatingly rigorous analysis in this post. I think this is one of those few topics in life that’s worth it. Other voices will never stop fiercely trying to live your life for you—you owe it to that little insecure character in the very center of your consciousness to get this right.

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And if you want to download this post for printing and offline sharing, you can buy it here.

The site 80,000 hours—dedicated to helping young, high-potential people make big career choices—is an awesome resource. The site is run by super smart, thoughtful, forward-thinking people, and can be digested in video or book format in addition to on their site.

I’ve been reading Seth Godin’s blog for years. Seth has a lot of wisdom in his head, and he doles it out in little bite-sized nuggets each morning on his blog (which I receive by email). A lot of Seth’s advice applies to career choices. Here’s an example (which I adapted into one of the cartoons in this post).

Eric Barker’s blog is full of actual data that can help with career choices, like this post on what makes a career fulfilling or this one on the importance of mentors.

John Venn really pulled something off here. A Venn diagram is the most obvious possible kind of diagram, and somehow, John Venn convinced everyone he invented it. And this is despite openly saying he didn’t invent it. Venn explains: “I began at once somewhat more steady work on the subjects and books which I should have to lecture on. I now first hit upon the diagrammatical device of representing propositions by inclusive and exclusive circles. Of course the device was not new then, but it was so obviously representative of the way in which any one, who approached the subject from the mathematical side, would attempt to visualize propositions, that it was forced upon me almost at once.”↩